Notes:

Content notes/warnings/spoilers: Underage Stiles as usual including references to solo acts when he’s under 16, masturbation, cross-dressing, boys in panties, come play.A/N: For Donnersun because she’s awesome, and also sick. Get well soon bb :)Thank you to Beckybrit for pre-reading and ItsAThinLine for a beta check.

Work Text:

Stiles can never really remember exactly how it happened.

A teenage boy having a healthy obsession with the underwear section of the Sears catalog was normal, yes? And so what if he actually spent about as much time looking at the bulging crotches of the guys as he did the mysterious smooth mounds of the women. It was easy to convince his fourteen year old self that it was for comparison only, to see how his own developing body parts measured up. Totally normal. He always turned back to the pages with the girls when he jerked off, because that’s what guys do.

He loved looking at the underwear, the pretty lace and beautiful colors of the shiny, silky fabrics. The mens' underwear was so dull in comparison, all navy and gray with the occasional burgundy, maybe some stripes if you’re lucky.

As for how Stiles came to actually acquire a pair of girls’ panties, well. That was a year or so later and was totally Scott’s fault. It was a dare and Stiles wasn’t going to back down from a dare and face the eternal shame and ridicule. And once he was inside the girls’ locker room he figured he might as well make sure he got the best trophy possible, so Lydia Martin’s locker was the obvious one to break into. Stiles just knew she’d have good taste in underwear. Sure enough he was rewarded with panties that were sexy-yet-classy and probably ridiculously expensive, made from deep emerald green satin trimmed with matching lace. He shoved his prize into his pocket and ran. And after showing them to Scott to prove he’d done the dare, he folded them carefully and tucked them back into his pocket and ended up taking them home. Well, what the hell else was he going to do with them?

Shortly after that Stiles started watching a lot of porn. While he watched he’d find himself looking at the panties that the women wore (before they got ripped off).

Then one day he remembered Lydia’s panties, that he’d kept balled up in a pair of socks at the back of his drawer and got them out. He held them in his hand while he jerked himself off. He let the silky fabric slip through his fingers, and used the soft scratch of the lace to make his nipples hard. But while he did it, his eyes ended up focusing on the guys on the screen instead of the girls (as they often did these days). The whole experience was basically an epic clusterfuck of sexual confusion. But when Stiles finally wrapped the satin around his dick and stroked himself with them, he came so hard that he didn’t really care anymore.

From that day on, the panties were a permanent fixture in Stiles’ masturbatory routine. The feel of them on his skin was enough to make him hard almost immediately and he nearly wore them out he jacked off with them so much. It’s a good thing they were easy to hand wash.

The first time Stiles actually put them on himself, he felt an uncomfortable mixture of ridiculous and unbearably excited. Even though he knew he was alone in the house he kept expecting the door to fly open and his dad to burst in. Stiles could see in his head the exact expression of stunned disbelief that would be etched on his father’s features. Because, yeah. Stiles looked kind of obscene in the panties. Stiles has slim hips and a perky little ass, so they weren’t a bad fit at the back. But at the front his erection bulged at an awkward angle, pulling the shiny satin tight where it was barely contained by the scrap of material.

He stood in front of his mirror and twirled slowly. And yeah, maybe it was weird that he had thoughts about how amazing the green looked against his pale skin, but it really fucking did. His cock twitched as he pressed his hand against it through the fabric and he bit his lip to suppress a whimper. That day he ended up on his knees in front of his full length mirror, panties tucked under his balls while he jerked off. He painted stripes on his mirror when he came.

It was a slippery slope into underwear addiction. They don’t warn you about that shit at high school. Just say no to panties kids, one pair will never be enough.

So, by the time Stiles was sixteen and all the crazy wolf shenanigans kicked off in his life, he had what could only be described as a collection (albeit a modest one) of lingerie. The internet is a wonderful thing and there are places that cater for guys who like the things that Stiles likes. Specifically panties, but panties that are designed for dudes. Stiles is a big fan of these specialist retailers because panties that are cut with guys in mind are way more comfortable in the balls department, and Stiles’ balls are very sensitive.

Stiles has also picked a team by now, realizing that his interest in womens’ underwear has nothing to do with any interest in actual women. No, Stiles is all about the cock now. He just needs to find someone in real life who he can test this new-found knowledge out on.

The panties are an alone-time thing only. Much as Stiles would love to be able to wear them out of the house, there’s no way on earth he’s going to risk that. Even leaving aside the whole school locker room thing, his best friend is a freaking werewolf now and has super senses like whoa. Better safe than sorry, who knows if panties smell different to boxer briefs? It’s not something that has come up in conversation with Scott.

So, panties at home only. And only when his dad’s out of the house, because Stiles is nothing if not cautious. The last thing he needs is for his dad to catch a glimpse of red lace or white polka dots on fuchsia peeking over the top of the waistband of Stiles’ jeans. Nope, he doesn’t want to be responsible for giving his dad a heart attack when he spends so much of his time trying to keep him healthy.

But today; today is a Stiles alone-time day. It’s a Sunday and his dad is working, Scott’s busy with Allison and Stiles has no plans. Well, that’s not entirely true. He has plans. But his plans pretty much consist of chilling out around the house while wearing his current favorite panties (red satin boyshorts with a subtle black lace trim). The plans also include wanking, probably more than once because it’s so much more satisfying doing it when his dad is out and he doesn’t have to try and be quiet.

Stiles isn’t very good at quiet.

He’s in the kitchen, crashing around as he washes up the pans from last night’s dinner. He’s ignoring his half-hard dick, but enjoying the awareness of it filling out the fabric of his panties, pressing against the denim of his jeans. It’s like foreplay with himself, the knowledge that a little later he can go up to his room and take his time getting off.

Stiles may be a person who normally lives at a fast pace, but slow, leisurely wanking is one of his favorite things. He loves to strip everything off -- except his underwear of course -- and really go to town. Sometimes he stands by the mirror on his wardrobe door, like that first time. Other times he stretches out on his bed, but he angles the wardrobe door so he can see himself. It’s not that Stiles is vain, far from it. He knows he’s pale and gawky, and a little scrawny. He doesn’t look anything like the sort of ripped, muscular guys that he finds hot. But he likes to be able to see his panties and his hand moving on his dick, his own come as he spills over his fist and belly (or the floor and even the mirror if he shoots hard enough.) It’s like his own little private porn show. And yeah -- he’s a pervert. But Stiles figures that everyone has their kinks and as long as it’s not hurting anyone else then what does it matter?

So there he is, up to his elbows in hot soapy water, dick filling in his pants with anticipation of his morning wank-plans. His oblivious human senses totally let him down as usual, and it’s not until he turns around and actually sees Derek sitting on one of the kitchen chairs that he realizes he’s not alone.

“Holy fucking shit!” Stiles leaps what feels like three feet in the air and clasps a hand over his pounding heart. “What the fuck, man? Doors... knocking... we’ve discussed this haven’t we?” Derek just stares at him impassively, all broad thighs spread in the kitchen chair and brooding film star good looks. But then his eyes narrow slightly and his look turns intent and curious. Stiles feels a flush creep over his whole body like warm honey being poured from the inside out. Werewolves had better not have some sort of x-ray vision sense that he hasn’t read about yet. Derek doesn’t look like he’s about to speak anytime soon, so Stiles does what he does best and fills the awkward silence -- well, it’s awkward for him. Derek looks completely unmoved by it of course, because Derek doesn’t do awkward.

“Why?” Stiles tries to control the itchy urge to start flapping his hands. “Why do you do this? This creeping around thing... Do you enjoy scaring people in general? Or just me specifically?”

Derek’s lips part and curve, white teeth gleaming against the dark stubble on his stupidly perfect jaw. It can only be described as a wolfish grin.

“You’re such a dick.” Stiles glares at him.

He turns and gets back to his dishes, determined to ignore Derek until he uses his words and tells Stiles what he’s actually here for. Stiles’ dick is annoyingly, persistently hard now. You’d think the shock of having a werewolf sneak up on him would have taken care of that problem, but no. Apparently Stiles’ dick is all in favor of mysterious, brooding, fuck-hot shapeshifters lurking in his kitchen. He has that itchy, prickly feeling between his shoulder blades, and he knows that if he turns around that Derek’s eyes will be on him. He shifts uncomfortably, wanting to adjust his erection in the too-tight-now panties, but there’s no way he’s going to draw Derek’s attention to anything that’s going on below Stiles’ waist. Nope. Not happening.

“Quit staring at me, you creeper.” He snaps without turning. Okay, so the ignoring didn’t go too well. But seriously, he’s had enough of this shit.

“Stiles.” Derek’s voice is soft and alarmingly close to his ear.

Stiles jumps again, splashing water on the front of his t-shirt. He whips around to face Derek, shaking the water off his hands and wiping them on the legs of his jeans. “Dude!” He protests, about to launch into more protests about human senses and their fallibility, and how it’s just not polite to keep doing this to people. But the words dry up due to the proximity of Derek and the strange intensity on his face.

Derek’s eyes move down Stiles’ body and come to rest on his crotch. Stiles wishes he’d worn a longer t-shirt because this one does nothing to hide the fact that he’s hard. His whole body feels flushed with shame and arousal and his knees are all wobbly. It’s a good thing he’s leaning back against the kitchen sink or he’d seriously have problems staying on his feet right now. His erection is trapped kind of sideways because he hasn’t been able to pull it up straight and it’s so fucking humiliatingly obvious. But apparently Stiles gets off on humiliation, because instead of getting the message and calming the fuck down his dick just twitches and leaks pre-come in his underwear.

Derek’s nostrils flare and Stiles feels even more blood rush to the surface of his skin as he blushes harder -- oh God, Derek can smell that -- and how is it even possible that he has enough blood left for a full body flush when it feels like all the blood in his system has been re-routed to his dick?

As awkward silences go, this one is reaching new levels of excruciating hideousness. But this time it’s Derek who breaks the silence.

“What type of underwear are you wearing?”

He says it without a flicker of irony; how is that even possible? Stiles has no idea how to answer the question. He knows his mouth is hanging open but he lacks the will to shut it. He just stares as Derek moves even closer, as close as he can get without actually touching Stiles. His nose is alongside Stiles’ cheek and he inhales deeply and his breath is warm as he lets it go.

“I can hear the fabric when you move, Stiles.” Derek’s voice is a low purr that makes Stiles shiver. “They sound different to what you usually wear, to what guys usually wear.”

“You have to be kidding me,” Stiles manages, a nervous quaver to his voice that he hates but can’t control. “You can hear people’s underwear? I don’t even know what to do with that information. God, your life must be so weird.”

Finally Derek touches him. Just the skim of his finger along the soft skin of Stiles’ belly as Derek hooks his finger in the waistband of Stiles’ jeans and pulls them away from his hip bone. Stiles looks down, paralyzed by arousal and mortification and sheer blind panic, and sees what Derek sees. Scarlet satin, black lace trim and the shape of Stiles’ cockhead pressing wet against the fabric, staining it dark like blood. Even Stiles’ human nose can smell it now.

Derek growls and Stiles just gasps out an insane gust of laughter, because this is a thing that’s actually happening. And he doesn’t know what the fuck’s going on here exactly, but Derek is pressed up against him now, and there’s definite grinding happening. It turns out that although Stiles may be the one who’s been caught wearing panties, he isn’t the only one with an awkward boner, and that makes him feel a whole lot better about this situation.

A whimpering noise escapes as Stiles drops his head back. He stares at the cracks in the kitchen ceiling, trying to ground himself. But then Derek licks his throat and his hand is rubbing Stiles’ dick through his jeans and Stiles moans, loud and long, like someone in a porno. He’s too far gone to be embarrassed anymore. He just needs to come. Apparently Derek seems to have that goal in mind too, because he’s sliding down Stiles’ body and tearing at the fly of his jeans and shoving them roughly down around his thighs.

He holds Stiles by the hips and pauses for a moment and Stiles dares to look down at him. Derek’s staring at the panties and he’s breathing hard and frowning. Stiles wants to smooth that frown away with his fingertips but he’s not brave enough to touch, not yet. Then Derek’s eyes flick up to meet his as he moves forwards, running his nose along the length of Stiles’ dick through the red satin. Derek’s eyes glow red too and Stiles just stares at him until Derek breaks their gaze and starts to mouth at Stiles’ cock. His breath is hot and his spit makes Stiles wet and it’s just all too fucking much.

“Oh my God,” Stiles manages, gripping the counter top with his hands and holding on for dear life. “You’re actually doing this. Okay then.”

Stiles has thought a lot about how his first sexual encounter might go. He’s imagined random strangers, he’s thought about Danny. He’s even fantasized about Jackson on occasion, because sure, the guy’s a total douche, but those abs and those lips... hell, Stiles is only human. But now he realizes that weirdly he’s never imagined this happening with Derek. Maybe because despite being pretty much Stiles’ perfect man in terms of physical perfection, Derek has always seemed so utterly unobtainable. But maybe also fundamentally because Stiles had always imagined that the first time he did any of this stuff it would be with another human.

Stiles looks down at Derek licking his cock and snuffling at his groin with a definitely more than human amount of appreciation. He feels the unnatural strength of Derek’s fingers gripping his hips as he holds him in place -- because it’s really hard to keep still when it feels this good -- and he suddenly realizes. His previous fantasies were total bullshit in comparison. This, this right here, is what he’s going to be jerking off to for the rest of his life. Derek hasn’t even got Stiles’ dick out of his panties yet and Stiles is about to jizz.

“Please,” he whines, and he’s not even sure exactly what he’s asking for. But Derek seems to know what he needs, because he hooks the red fabric under Stiles’ balls and pauses briefly to nuzzle them, before licking a hot, wet stripe up Stiles’ dick. Then he parts his lips and sucks Stiles down into the heat of his mouth before pulling back to focus on the head. Derek makes a sound that’s half-growl half-hum and it vibrates though Stiles’ cock and down into his balls and he can’t hold back anymore. He clutches Derek’s head with both hands, the hair thick and surprisingly soft between his fingers. Stiles’ hips jerk and snap as he comes, pushing into Derek’s mouth, hitting the back of his throat hard and crying out with the shocking pleasure of it. His legs are shaking and giving out beneath him and he slumps down, taking Derek with him until Stiles is slumped awkwardly with his ass on the kitchen floor leaning back against the kitchen cupboard.

When Stiles is able to focus again he looks down and Derek’s lying between his thighs, still sucking and swallowing with a dedication and intensity that’s really quite awesome. He stops when Stiles’ dick starts to soften, gives him a last long lick that makes Stiles’ half-hard cock twitch feebly, and kneels up, pulling his own fly open to get at his dick.

“Fuck, Stiles,” he mutters, fingers shaking as he struggles with his zipper. His voice is rough and hoarse, and Stiles did that to him. Stiles’ cock in Derek’s throat did that to him. Stiles thinks that fucking Stiles sounds like an excellent idea actually, but it doesn’t look like Derek can wait to do anything too complicated right now. Maybe another time, Stiles hopes.

Derek shuffles forward, straddling one of Stiles’ legs so he can get close, and then he’s right there. Derek’s dick -- his beautiful uncut dick -- is right in Stiles’ personal space in a way that he’s all in favor of. Derek’s stroking himself firmly, and although Stiles is more than a little mesmerized by the way his foreskin slides with the movement he doesn’t want to just be a spectator for this. His mouth drops open and his hands are on Derek’s ass, pulling him closer. “Please,” Stiles whines, all greedy and needy. He feels like he’s going to die if he doesn’t get to feel Derek’s cock in his mouth.

Cause of death: denied Derek’s dick. It could be a thing.

Luckily Stiles doesn’t have to find out if it’s possible to die from lack of a dick to suck because Derek’s sliding the head along his bottom lip, making Stiles whimper for more as he slips his tongue out to lap at the sticky wetness. Derek teases him with one more pass, tapping Stiles’ lower lip to make it drop, and then he pushes in deep and slow and starts to move as Stiles does his best to lick and suck and do stuff that he hopes feels good to Derek.

Stiles has no control in this position. Half-sitting, half-lying with his head jammed back against the cupboard under the kitchen sink he can only trust Derek not to choke him. Because, yeah, Derek’s cock is pretty big and it feels amazing in Stiles’ mouth, but Stiles has never done this before and practicing on a banana only prepares you for so much. Bananas don’t care about teeth for instance, and Stiles is suddenly very aware of just how many teeth he has, and how hard it is not to scrape Derek with them. But Derek’s cock feels totally awesome compared to a banana. It’s hot and silky and tastes of sex and -- oh Jesus -- bananas definitely don’t make appreciative, desperate-sounding noises like that.

Derek’s hand is on Stiles’ head, ruffling the fuzz of his hair. It moves to his cheek, surprisingly gentle and Derek moans again as he presses his thumb into the hollow of Stiles’ cheek and feels the movement of his cock. Stiles hums back around his mouthful of dick, encouraging him, trying to let him know that this is good. Stiles likes it too.

Derek’s hips are moving faster now, the muscles of his ass tight under Stiles’ eager fingers. Derek’s hand is back on Stiles’ head, slipping behind to cradle it, protecting him from the hard wood of the cupboard as Derek fucks his mouth.

Stiles feels it on his tongue, the shiver-pulse and swell of Derek’s dick as he’s about to come and he braces himself, ready to swallow. But Derek pulls back and grips himself tight in his fist, letting his come spurt onto Stiles’ parted lips and chin and a little on his cheek. Stiles’ licks his lips instinctively and Derek mutters, “Fuck,” still coming with another jerk of his cock in his hand and blurt of white at the tip. Stiles licks that away too. Derek’s come tastes pretty much like his own -- and yes, of course he’s tasted it, it’s normal to be curious about these things -- no special werewolf flavor or anything unexpected.

Derek drops down now, supporting his weight on both hands as he lowers his head. His breath is hot on Stiles’ lips and then Derek’s licking him clean, his tongue sweeping the remaining come from Stiles’ chin, then cheek, then finally his lips. And it’s so desperately dirty and wonderful that Stiles moans and his hands find their way into Derek’s hair. Somewhere along the line, licking turns into full-on mouths-open, tongues-tangling kissing and Stiles finds himself thinking: so actually this is how I’m going to die.

Cause of death: asphyxiation by making out with a werewolf.

He’s actually okay with that.

It turns out that werewolves need oxygen too because Derek finally pulls away and stands up, offering a hand to Stiles and yanking him up too. They rearrange their clothes and avoid each others’ eyes for a moment and somehow they’ve gone from the amazingness of the sex to the weird oh-my-god-we-just-did-sex-stuff aftermath -- not that Stiles is familiar with it himself, but he’s heard it described by others and turns out that it’s just as fucking awkward as they say.

Stiles being Stiles, the silence gets to him pretty quickly and makes words start tripping out of his mouth before he has time to engage any sort of verbal filter.

“So... uh... that happened. That actually just happened.” He runs his hands through his hair and then shakes his head, gesturing between them wildly. “I mean... what did just happen? Because I had no idea... I never... I didn’t even know you liked dudes!”

“So I see,” Derek grins. It’s disconcerting. He smiles so rarely and it’s such a good look on him that Stiles has another knee-wobble moment and finds himself talking again before he can stop and remind himself to be cool.

“So this,” he gestures between them again. “This thing... what is this?”

Derek takes a step towards him and Stiles jerks back, nervous, bumping into the kitchen counter. Derek moves closer still, and suddenly they’re almost back where this all started.

“It’s whatever you want it to be,” Derek shrugs. “Do you want it to be a thing?”

He’s so close that Stiles can feel his warm breath on his face, the heat of Derek’s body. He itches to touch him again. “Yes,” he swallows hard.

“So... do you have plans for the rest of the day?” Stiles’ eyes drop to where Derek’s hands are now resting on Stiles’ hips. “Because my plans mostly involved chilling out around the house and jerking off, so...”

“I could help you out with that.” Derek’s voice is warm with humor.

Stiles’ eyes flick back up at that and this time he finds a definite smirk rather than a grin. It turns out that that’s quite a good look on Derek too.

Notes:

I also write original m/m fiction. You can find out more about my writing here.